N⁶-benzoyl-5'-O-[(tert-butyl)diphenylsilyl]-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-3'-O-[(tert-butyl)diphenylsilyl]-2',5'-dideoxythymidine

Base Information

• Chemical Name: N⁶-benzoyl-5'-O-[(tert-butyl)diphenylsilyl]-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-3'-O-[(tert-butyl)diphenylsilyl]-2',5'-dideoxythymidine
• CAS No.: 206982-57-2
• Molecular Formula: C₆₁H₆₉N₇O₉SSi₂
• Molecular Weight: 1132.5
• Mol file: 206982-57-2.mol

Synonyms:N⁶-benzoyl-5'-O-[(tert-butyl)diphenylsilyl]-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-3'-O-[(tert-butyl)diphenylsilyl]-2',5'-dideoxythymidine

Chemical Property of N⁶-benzoyl-5'-O-[(tert-butyl)diphenylsilyl]-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-3'-O-[(tert-butyl)diphenylsilyl]-2',5'-dideoxythymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N⁶-benzoyl-5'-O-[(tert-butyl)diphenylsilyl]-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-3'-O-[(tert-butyl)diphenylsilyl]-2',5'-dideoxythymidine

There total 13 articles about N⁶-benzoyl-5'-O-[(tert-butyl)diphenylsilyl]-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-3'-O-[(tert-butyl)diphenylsilyl]-2',5'-dideoxythymidine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C61H69N7O7SSi2 → N6-benzoyl-5'-O-[(tert-butyl)diphenylsilyl]-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-3'-O-[(tert-butyl)diphenylsilyl]-2',5'-dideoxythymidine (206982-57-2)

Guidance literature:

With Oxone; sodium acetate; In tetrahydrofuran; methanol;

DOI:10.1021/ja972768y

Reference yield:

(2S,3S,5R)-5-(6-Amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-carbaldehyde (157729-47-0) → N6-benzoyl-5'-O-[(tert-butyl)diphenylsilyl]-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-3'-O-[(tert-butyl)diphenylsilyl]-2',5'-dideoxythymidine (206982-57-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 79 percent / NaBH₄ / ethanol; tetrahydrofuran / 2 h / 20 °C

2: 79 percent / PPh₃; DIAD / tetrahydrofuran / 2 h / 0 - 20 °C

3: N,N-dimethylpyridin-4-amine / pyridine / 1 h / 20 °C

4: 937 mg / aq. NaOH / pyridine; ethanol / 0.17 h / 20 °C

5: Cs₂CO₃ / tetrahydrofuran; dimethylformamide / 20 °C

6: 983 mg / Oxone; AcONa / tetrahydrofuran; methanol; H₂O / 2 h / 20 °C

With dmap; Oxone; sodium hydroxide; sodium tetrahydroborate; di-isopropyl azodicarboxylate; sodium acetate; caesium carbonate; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; ethanol; water; N,N-dimethyl-formamide; 2: Mitsunobu reaction;

DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1

Reference yield:

9-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}adenine (206982-53-8) → N6-benzoyl-5'-O-[(tert-butyl)diphenylsilyl]-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-3'-O-[(tert-butyl)diphenylsilyl]-2',5'-dideoxythymidine (206982-57-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 79 percent / PPh₃; DIAD / tetrahydrofuran / 2 h / 0 - 20 °C

2: N,N-dimethylpyridin-4-amine / pyridine / 1 h / 20 °C

3: 937 mg / aq. NaOH / pyridine; ethanol / 0.17 h / 20 °C

4: Cs₂CO₃ / tetrahydrofuran; dimethylformamide / 20 °C

5: 983 mg / Oxone; AcONa / tetrahydrofuran; methanol; H₂O / 2 h / 20 °C

With dmap; Oxone; sodium hydroxide; di-isopropyl azodicarboxylate; sodium acetate; caesium carbonate; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; ethanol; water; N,N-dimethyl-formamide; 1: Mitsunobu reaction;

DOI:10.1002/1522-2675(200209)85:9<2777::AID-HLCA2777>3.0.CO;2-1

upstream raw materials:

benzoyl chloride

(2S,3S,5R)-5-(6-Amino-purin-9-yl)-2-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-3-carbaldehyde

9-{(3'R,4'S)-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-3'-C-(hydroxymethyl)-β-pentofuranosyl}adenine

9-{(3'S,4'S)-3'-C-[(acetylthio)methyl]-5'-O-[(tert-butyl)diphenylsilyl]-2',3'-dideoxy-β-pentofuranosyl}adenine

Downstream raw materials:

N⁶-benzoyl-2'-deoxy-3'-de(phosphinicooxy)adenylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine

N⁶-benzoyl-2'-deoxy-3'-de(phosphinicooxy)-5'-O-(4,4'-dimethoxytrityl)adenylylmethylenesulfonylmethylene-(3'->5')-2',5'-dideoxythymidine